I can provide more blocks of text, but that might not be the best solution. Everything in terms of plotline and major events is here. Right now, it would need revisions: what looks like it might work, what doesn't, what parts should be cut or elaborated on, etc. This kind of criticism is not something I can easily apply to my own work.

I have tried to summarize and structurize the current questplans so it's easier to discuss details. I made this little graph of the current quests and how they branch out. I have amended the description of the first quest according to the discussion that followed it.

In Ebonheart, the NPC Titus Corilex (member of the EEC) offers the player a job as a guard on an ebony shipment heading to Cyrodiil, avoiding the absurdly high prices and border tariffs, as well as any investigations into the player's past [Corilex should also offer “normal” fast travel services to Stirk after this event concludes]. Along the journey, the ship [the Star-Marked] is attacked by pirates.

The player defeats the pirates and goes to talk to the captain, who decides to dock in Stirk for repairs. Once the player leaves the ship there, the captain asks them to report the pirate attack at the harbor office, and hands them the pirate note which they found on one of the pirate's bodies ("Hey, can you report this for me? I got enough on my mind without dealing with the bureaucracy"). From there on, the player is free to wander the island, or go to the census office immediately.

At the Cencus office Lysandro Draco asks the player some questions based on the tutorial/character creation [name, race, class], and gives identification papers to present to Syro Neminus in Town Hall.

The holder of this document is hereby identified as %PCName, %PCRace, %PCClass, passenger on the Star-Marked, shipwrecked and cast ashore on the isle of Stirk, questioned and confirmed of identity by the Census & Excise Office of the Prefecture of Stirk, province of Cyrodiil

signed,
Lysandro Draco
Agent at the Stirk Imperial Census & Excise

Neminus informs the player that the town's Prefect, Cocious Hassell, wants to speak to them about the pirate attack. Hassell is trying to stop the pirates, and wants information about their methods. In talking to Hassell, the player can hand over the pirate note. Hassell doesn't trust the locals to act in his behalf, and offers the player a temp job as an investigate agent on his behalf.

2 - The Westernmost Shore

Hassell needs two things:

The pirate note mentions a merchant in Stirk. This can only be Victus Pilious, wealthiest man on the island and a personal enemy of Hassel. The player has to interview Victus, ask try to figure out what his connection is.

The note also mentions a secret contact in town. Hassell wants the player to ask around in lower class establishments, to gauge the loyalty and attitude of the locals. It would be bad news if people started sympathizing with the pirates.

Before the player can visit Pilious, they must get past his secretary, Estarria, who demands a letter of introduction. The player can get one from Hassell, but this causes Estarria to delay the meeting for two days. They can try and bribe Estarria, but he will reject their boorish, provincial methods. Alternatively, the player can persuade/question the servants in Pilious' manor (or listen to Aenais Geraneus' rumors), who know that Estarria has a weakness for Aliyew. Bribing him with a bottle allows instant access to Pilious [hints at the complexity of Heartlands social and political relations – both Estarria and Pilious should reflect Heartlands values].

Pilious denies any connection to the pirates, but also immediately offers the player a higher-paying job (“government service is no way to get ahead in life”) if they investigate the matter on his behalf, claiming that Hassell is too incompetent and tangled in bureaucracy to be of use. He will urge the player to return to him once they have finished this job for Hassell.

To investigate the pirate contact, the player must talk to the locals in the Old Seawater and Sload's Tale Inn. The locals consider Hassell and Pilious untrustworthy Nibenese outsiders. The workers support Hassell because he pays their wages, nothing more. Mention is made of the old Helvor family: many older inhabitants still come to Vilina Helvor with information, and she has a good insight into the local population. The player is encouraged to visit the Helvors. According to Vilina, the island's political situation is to blame: people don't trust outsiders, and need the steadfast rule of a Colo-Nordic family. Hassell and Pilious are only out for their own interests, and cannot be trusted to act in the town's interest. Like Pilious, she asks the player's help.

After this, the player returns to Hassell to report their findings and receive a small payment. If the player mentions the counter-offers from Victus and Vilina, Hassell will increase the proposed payment for your services and restate his own case, claiming to be be the only one authorized by the Empire to deal with this crisis.

This ends the quest. All three NPCs now have a unique greeting, asking the player if they are willing to work exclusively for them. If the player agrees with any of them, they are locked into that character's questline. [It should be clear to the player that this leads to mutually exclusive quests, Great House style].

Hassell: rightful rule, law, and the ideals of he Empire. This questline is the most straightforward and least morally conflicted.

Pilious: money and influence. Players should take this questline out of self-interest and notions of realpolitik. Pilious offer power for those who don't mind getting their hands dirty.

Helvor: might makes right, authoritarianism, the rule of unchecked power. This is the most morally dubious questline, since the player will end up working with the pirates. It should be implied from the start that Vilina has a “the end justifies the means” attitude, and that here interest lies not so much with stopping the pirates as with restoring the rule of the Helvors.

A1 - Hassels Questline Stage 1

Hassel does not trust Pilious' denial, and tasks the player to find out more about his past. One person who might help them is Geval Ugenring, the former Prefect of Stirk, who has a personal vendetta against Pilious. Problem is, Ugenring is demented and paranoid, a nervous wreck after the burdens of his office became too much for him. Ugenring readily admits that he has a file on Pilious, collected from agents-for-hire and old friends on the mainland. However, he has hidden it somewhere in a fit of paranoia, and cannot in his current state say where it is. The player must find a way to clear Ugenring's insanity.

There are several healers on the island who offer cures:

Tynellion, the priest in the Temple, offers a blessing of Kynareth.

Sharli, the local healer/apothecary, sells a normal potion of restore intelligence (restocking in case the player drinks it himself).

Dandre Aurilie, the weird alchemist, has an experimental salve.

Each of these cures has to be found and applied to Ugenring. Ugenring himself gives suggestions where cures can be found, and his condition improves after each one. After the three cures, Ugenring still does not remember where he left the papers: he suggests looking around in the harbor for some sailor or trader who might sell cures.

The player is referred to Haron the Peddler, a sailor who hawks badly enchanted trinkets. He offers a Ring of the Derelict Mysteries, an artifact of the Nibenese Sheogorath cult [the legality of Daedric cults in Cyrodil can be pointed out here]. Giving this to Ugenring drives him completely insane again, but does make him remember where he hid his files: in the grain storage opposite of Town Hall. The files are written in an old Imperial cypher.

Player brings the files back to Hassell, who sets about decoding them.

A2 - Hassels Questline Stage 2

Ugenring's files suggest that Pilious and Iarnu were once business partners, before Iarnu was convicted. They also show that Pilious has secretly been sabotaging Hassell's efforts to defend the city. The proof, however, is too scant and anecdotal, so the player has to find additional incriminating evidence.

For a while now, Pilious has flaunted Hassell's authority by refused the guards from inspecting his ships. Recently, a Khajiiti-crewed ship, the Snarleyowhl, has arrived in the harbor on an assignment for Pilious, and Hassell has reason to believe there is something illegal going on there. He tasks the player to infiltrate the ship and look around.

On board, the player can find some evidence of fraud in the logbooks, or, if they look carefully, a stash of moon sugar and skooma in a hidden compartment. Finding the second secret gives a better reward. Hassell can use this as blackmail material to keep Pilious at bay for a while – though not forever, as Pilious will probably shift the blame to his subordinates.

A3 - Hassels Questline Stage 3

One of Hassell's scouts, Valanyra [Altmer woman near a camp on the island] has sent a message: she spotted a small pirate sloop entering the cove beneath Wormusoel. The player has to go to her camp for more information. Valanyra believes the pirates have a secret passage in the cove, perhaps used by their town contacts for provisions. The player has to enter the cove through the seaside entrance, and fight several pirates there. Using a key found on one of the pirates, they can enter the secret passage.

The player follows the passage to the end, dealing with the pirates inside, until they exit at the Helvor Crypt in the graveyard [the secret passage here should be locked from the other side, to prevent sequence breaking]. The player then reports the existence of this tunnel to Hassell.

A4 - Hassels Questline Stage 4

The fact that the pirate supply tunnel goes through the Helvor crypt incriminates the Helvors, who have the only keys to this place. Go to the Helvor family house and interrogate those that live there. A bit of dialogue detective work reveals that the Quillians, an old pair of servants to the family, were responsible. Their son is a member of the pirate gang, and they supplies them without the Helvors knowing [in the Helvor questline, it turns out that they were working under orders from Vilina, but this should only be hinted at here].

A5 - Hassels Questline Stage 5

Hassell's scouts have reported that the pirate ship has docked at their camp on the northern islands [pirate ship and pirates there should initially be disabled]. Hassell congratulates the player for their help, and offers them to lead the assault on the pirate camp. Playe can accept, or ask time to prepare.

Once the player accepts, they are teleported to the southern beach near the pirate camp [pirates and ship are now enabled – do not enable before then]. They are accompanied by 4 or 5 Gold Coast Guards [same principle as the Ward of Akavir assault]. The player attacks the pirate camp, works their way across the hill, and enters the pirate ship, where they can fight with Iarnu.

After the fight, the player can use Iarnu's key to unlock the lower deck with the pirate treasure. Hidden somewhere on board is also Iarnu's secret diary, which contains more incriminating information about Pilious: it turns out that Iarnu was once an honest merchant, but was framed for fraud by Pilious and forced to become a pirate. Iarnu wanted to sack Stirk, destroy everything that Pilious had built there, and murder him. The player can give this book to Hassell, or use it to blackmail Pilious. [Finding the book should be hard, an optional bonus].

B1 - Pilious Questline Stage 1

First, Pilious wants to discredit his opposition. According to his agents, Prefect Hassell is petitioning his friends and superiors on the mainland to get a better assignment. The player must break into Hassell's manor (which is patrolled by guards), and exchange a scrollcase with letters to be sent to the mainland with an identical one that Pilious had falsified. This quest also serves as a test of the player's loyalty.

B2 - Pilious Questline Stage 2

Hassell receives his information about the pirates from a scout out on the island, an Altmer adventurer called Valanyra. The player has to persuade her to work for Pilious instead, and feed Hassell false information. This can be done through persuasion, intimidation, or trickery (dialogue skill checks).

B3 - Pilious Questline Stage 3

One of the fishermen informed Pilious that Caspus Quillian, a servant of the Helvors, has been acting suspicious. They saw him signaling with a lamp towards the sea, and walking around late at night. The player has to lie in wait near Helvor Manor (Fargoth's Hiding Place-style) and secretly follow him. Quillian enters the crypt in the graveyard, and stays there for about two hours. If the player follows him inside, this leads to a confrontation near the entrance (forcegreeting?). Quillian admits that his son is a member of the pirates, and that he is supplying them (the same lie he tells in the Hassell questline). He also tells the player that they are mistaken to trust Victus Pilious, as he has betrayed many of his business partners in the past. The player can threaten him (personality check) or simply kill him to get a key to the door at the other end of the crypt, which leads to the secret pirate supply route (This is the same tunnel the player follows in the Hassell questline, but from the other side). Along this way, they encounter a small pirate camp.

B4 - Pilious Questline Stage 4

Once the player has followed the supply route to the cove beneath Wormusoel, the quest updates and they can return to Pilious to report the existence of this path. The player has the option to mention what Caspus Quillian said, and inquire after the connection between Pilious and Iarnu. Pilious decides to entrust the player with the whole story: he and Iarnu were once business partners in a plantation in one of the beastmen provinces. Pilious, overcome by greed, indulged in fraud and corruption, framing Iarnu for his misdeeds and running off with the profits, which he used to set up his business on Stirk. However, Pilious now claims to be a reformed man, trying to repent for his past crimes by providing for the people of Stirk. Iarnu has become a murderer and a pirate, and must be stopped at all costs. Alternatively, the player can neglect to ask this of Pilious, in which future dialogue interactions should reflect that they do not really know (or care?) what is going on.

Regardless of what is discussed, Pilious sends the player away for a day or two. With the pirate's supply line disrupted, it will only be a matter of time before they have to dock at their northern base. Then, Pilious promises, the player will lead his mercenaries into battle.

B5 - Pilious Questline Stage 5

After a day or two, the player receives a panicked message (messagebox pop-up in any exterior cell called "Stirk", or perhaps a scripted mercenary who runs up to the player to inform them - whatever works best) asking that they join him in his manor immediately. Pilious admits that he had received notice that the pirates had docked, but, in his impatience and distrust, did not wait for the player before launching his assault. Now, a group of the pirates has escaped and are hiding somewhere in the island. The player is tasked to travel to the pirate camp, and find any clues that could tell where the pirates are hidden.

In this instance, the pirate camp is a burned-out ruin, infested with scavenging animals (rats, etc.). Inside a pile of refuse, the player discovers a scrap of Iranu's burned logbook, which mentions the name and adress of his lover, who lives in a Stirk apartment. The player must return to Stirk and kill the surviving pirates and their leader, who are holed up in this apartment.

C1 - Helvor Questline Stage 1

Above all else, Vilina wishes to discredit Victus Pilious. While Pilious, a Nibenese merchant, is known to be dismissive of nobility, he secretly covets a title of his own and the respect that it brings. To this end, he is courting Ledaia Pelladia, a noblewoman who lives in seclusion on the island. Vilina asks the player to sabotage their courtship. High-persuasion players can convince Pelladia to help Vilina by spying on Pilious (by appealing to their shared nobility over a 'lesser' merchant), or trick her by presenting themselves as a representative of a rich Hammerfell prince (requiring, among other things, a fine set of clothing and an expensive gift). Less refined players can simply threaten or kill her. Killing her will not actually lose favor with Vilina, who approves of your pragmatism.

C2 - Helvor Questline Stage 2

To further discredit Pilious, Vilina wants you to break the bonds of trust between Pilious and the dockworkers and fishermen. Most laborers on the island work for Pilious' firm, and they are loyal to him (and their paycheck). Gaius Tragia, the unofficial leader of the dockside people, even has a granddaughter who works as a servant girl in Pilious manor. Vilina wants you to frame Tragia's granddaughter for theft, which will get her fired from the manor. Afterwards, the player has to approach Tragia and offer for the girl to come work in Helvor manor, as an act of charity and goodwill. This will cause public opinion to sway in favor of the Helvors.

C3 - Helvor Questline Stage 3

Vilina is pleased with your performance and, judging you to be suitably loyal, she explains part of her master plan: it is she who hired and supplies the pirates, all the while making sure that the Navy patrols never reached Stirk. Her plan is to disrupt the affairs of Hassell and Pilious, out them as self-werving and powerless fools, and then regain control over the island by having her (unknowing) brother lead the citizens of the town against a pirate attack on the harbor, killing them all, and restoring the rule of Helvor on the island.

The player has a number of options: they can keep it professional (don't care about politics, just want to get paid), affirm Vilina's actions and her noble right to rule, reluctantly admit that this is probably what's best for the island, or refuse to cooperate. If the player chooses the latter, Vilina will offer to double the reward, while explaining that, due to their outsider status and recent involvement, nobody on the island would believe them or trust them in this matter. It would also be better for a capable person like the player to handle this intrigue, since otherwise the (now inevitable) pirate attack could make a lot more victims. If the player continues to refuse, the quest simply ends here.

If the player agrees to continue aiding Vilina, she will send them out to the graveyard at night, to exchange some supplies for several pouches of gold with a representative of the pirates. This will seal their involvement in the matter.

C4 - Helvor Questline Stage 4

Prefect Hassell is becoming suspicious about the pirate supply line and Pilious' recent misfortunes. In order to distract him from the affairs of the Helvors, Vilina asks the player to lay a false trail of documents and gold in the archives and warehouses of the Census Office, incriminating the clerk Octavio Capillius. Afterwards, the player has to approach Lyasandro Draco, the leader of the Office, and convince her to investigate Capillius. This will lead to Capillious being arrested, or, if the player mishandles the investigation and confrontation, to Capillius attacking them and getting killed.

C5 - Helvor Questline Stage 5

According to Vilina, the pirates are still too reluctant to risk an open assault on the harbor (justified, since they would not survive this). She asks the player to go talk to them directly, giving them the coordinates of the pirate camp. Before you leave, Marin Quillian, one of the Helvor servants, comes up to you and asks that you deliver a message to their son, who is part of the pirate crew. She asks that the player warns him not to take part in the pirate attack, to save his life.

The pirates know you from the contact before, and are warned of your arrival: as such, they do not attack. The player has to convince captain Iarnu (through persuasion and/or trickery) that the town is weak and ripe for plundering. Additionally, a number of pirates require your help: one of them wants a better sword, another wants some potions of restore health, etc. Additionally, this is the only chance for the player to deliver a message to the Quillian son. If all demands are met, captain Iarnu will agree to attack.

C6 - Helvor Questline Stage 6

Once the player returns, Vilina says she will send out her brother, Gracchus, to gather the able warriors among the dockworkers. She invites the player to stay with her in the mansion and wait for the attack. After a couple of hours waiting/sleeping, the player can exit the house: in front of the building is Gracchus Helvor, accompanied by six or seven armed dockworkers (however many the engine can handle). They are all scripted to walk to the harbor. In the harbor, a couple of sloops, some damage (burning trash?) and pirates have appeared (all the pirates encountered in the northern pirate camp, including Iarnu). A fight breaks loose between the dockworkers and the pirates. The quest updates when all the pirates are dead. The player can return to Vilina for their reward.

Additionally, if Gracchus Helvor dies during the attack (something that should be made a likely occurrence through level/equipment) Vilina will still be pleased and give the player their reward. If the player confronts her about this, Vilina will admit that she believed it likely that Gracchus would die, and that she knowingly sent him to his death. Stirk will be in more capable hands with her in charge, instead of her simple-minded brother. As an extra reward, she offers the player her brother's old sword (or something like that).

Thanks, this does look a lot better. One thing to note is that the ship on which the player sails in/gets pirate attacked should be the Magnificent, which is the middle ship in Stirk's harbor. The interior can be used during the pirate attack, and the captain should be Jafan, an NPC who currently resides in the Sload's Tale Inn.

I agree that quest complexity is probably a bit too much: think of this as the rough draft in need of trimming. Ideally, we should simplify at least a couple of these quests, as long as the basic storyline of each one is preserved. In short, each chain is as follows:

Hassell: player has to discredit the opposition, figure out who the traitors on the island are, and follow their tracks back to the pirate lair.

Pilious: player has to discredit the opposition, figure out who the traitors on the island are, and discover the old connection between Pilious and the pirate captain. They also have to hunt down the pirates after Pilious' men bungle the assault.

Helvor: player has to prove themselves loyal by discrediting the opposition. Once this is done, the true nature of the quest is revealed: aid the Helvors in playing the pirates and the town officials against each other. Convince the pirates to attack and stage a heroic defense of the town, culminating in restored honor for the Helvors.

After reading through Hassels questline, I don't see much potential for simplification without taking away from the story.

The stage I'm unsure about is the one where the player walks into the Helvor Manor to interview the people in there. It sounds a bit silly to me to go to them asking: Hey do you secretly support the pirates? Moreover that step does not really impact the last step in the storybranch in any way.

At least, I would suggest changing the players task, so he will be tasked to investigate rather than doing a direct confrontation. Or if it is supposed to be a direct confrontation, it should be more of a thing where the player walks in with a search warrant and authority.

Regarding the very first part of the MQ: it would cost 429 gold to Travel (service) from Ebonheart to the Stirk docks. The service could be added to Titus Corilex (making him more of a generic captain) who would then refer you to an EEC NPC in Ebonheart if you can't afford the trip. The new EEC NPC would start the first quest as envisioned.

Titus Corilex would have his travel dialogue replaced with a travel service (fast travel) to Stirk.

The quest start upon arriving on Stirk (by the boat fast travel, only the first time) via a ForceGreeting from a nearby sailor. Something about having to visit the Census and Excise bureau for a quick inspection, local authorities being paranoid. The Census officer then directs the player to the pirate issue (as do some local rumors).

"2.5 outcomes":
- Player sides with the Prefect, respects authority of the Empire, defeats the pirates and brings the corruption of the other parties to light
- Player sides with the merchant-prince, rakes in the money, defeats the pirates and sabotages/blackmails the other parties
- Player uncovers the corruption of the local nobility, but decides to support them anyway, restoring them to greatness by cooperating in their scheme

The last one being more of an optional, "join the 6th house" path, maybe not as fully fleshed out as the others.

Vilina helvor, the Baron's sister, is actually funding the pirates in a complicated scheme to restore honor and respectability to her clan. It's more morally ambiguous than the other two. Depending on the way the player sleuths the plot, it might not be as obvious to side with her as opposed to the other two. Although in the end she does plan to double-cross and kill the pirates.